US3174933A - Lubricants, metal-working agents, and hydraulic liquids - Google Patents

Lubricants, metal-working agents, and hydraulic liquids Download PDF

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US3174933A
US3174933A US6377A US637760A US3174933A US 3174933 A US3174933 A US 3174933A US 6377 A US6377 A US 6377A US 637760 A US637760 A US 637760A US 3174933 A US3174933 A US 3174933A
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metal
hydroxyalkylated
lubricants
water
working agents
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Klein Alfons
Kauczor Hans Werner
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/74—Sulfur atoms substituted by carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/08—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/241—Manufacturing joint-less pipes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/242—Hot working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/245—Soft metals, e.g. aluminum
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles

Definitions

  • the present invention relates to the use as lubricants, metal-working agents and hydraulic liquids of hydroxyalkylated mercaptans.
  • the hydroxyalkylated mercaptans which are obtained by reacting Z-mercaptobenzthiazole or its substituted products with ethylene oxide, propylene oxide and/or epichlorhydrin in a molecular ratio of 1 to at least 5.
  • These hydroxyalkylated 2-mercaptobenzthiazoles are applied as such or in the form of their solutions in water and/ or hydrophilic organic compounds.
  • Attention is called, for instance, to Gluesenkamp, US. Patent No. 2,498,617, filed July 2, 1947, and to Harle, US. Patent No. 2,721,177, filed March 30, 1953.
  • Suitable representatives are for example ethylene glycol, diethylene glycol, triethylene glycol monoacetate, dimethyl formamide, methyl ethyl ketone, furthermore polyethers such as are obtainable for example by the polymerisation of 1,2- and/or 1,4-hydroxy compounds, by polycondensation of glycols or glycol mixtures, by conversion of glycols or glycol mixtures with aliphatic dihalogen compounds or by conversion of monoor polyhydric alcohols with 1,2- and 1,4-hydroxy compounds.
  • the ratio between the hydroxyalkylated Z-mercaptobenzthiazoles and the solvents to be considered may vary within wide limits: in many cases a content of 0.5 percent by weight of the hydroxyalkylated Z-mercaptobenzthiazoles is sufficient. Suitable proportions can easily be ascertained as the case may be.
  • hydroxyalkylated Z-mercaptob-enzthiazoles as Well as their solutions in water and/or hydrophilic organic compounds possess an excellent lubricating effect not only in the field of hydrodynamic lubrication but also in the field of maximum friction.
  • the hydroxyalkylated Z-mercaptobenzthiazoles in the form of their aqueous solutions can very successfully be applied in metal cutting because of their high efficacy in the field of maximum friction; they are transparent and do not lead to demixing so that the work pieces can satisfactorily be observed during treatment.
  • the hydroxyalkylated Z-mercaptobenzthiazoles or their solutions in water and/ or hydrophilic organic compounds can also be successfully applied in non-cutting metal-working. Thanks to their good compatibility with water they can easily be removed from the work pieces after treatment is completed. It is noteworthy that the hydroxyalkylated products do not give rise to cloudiness in hard water due to the formation of insoluble calcium compounds and that they can not only be used in a neutral but also in an acidic or alkaline medium.
  • the agents according to the present invention can also be admixed with defoaming agents, anticorrosives or with agents increasing the viscosity of the liquids.
  • the improvement consisting in applying to an object being worked a solution consisting essentially of a major amount of water and an active lubricating amount of a compound having the formula wherein X is a member selected from the group consisting of chloro and hydrogen and Y is a member selected from the group consisting of methoxy, nitro, chloro and hydrogen; when X is chloro, Y being defined as hydrogen, and when X is hydrogen, Y is defined as hydrogen, nitro, chloro and methoxy; and n is an integer of 3-18.
  • the improvement comprising employing as a lubricant an aqueous solution containing a major amount of Water and about .5%3% by weight of a compound having the formula 01- s-o,H.0- o,nlo) volition NO s wherein n is an integer of 3-18.
  • the improvement comprising employing as a lubricant an aqueous v 0 solution containing a major amount of Water and about .5 %3% by weight of a compound having the formula 5.
  • the improvement comprising employing as a lubricant an aqueous solution containing a major amount of water and about .5 %3% by Weight of a compound having the formula wherein n is an integer of 3-18.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Description

United States Patent C) ice tion of Germany No Drawing. Filed Feb. 3, 1960, Ser. No. 6,377
Claims priority, application Germany, Feb. 18, 1959, F 27,734 Claims. (Cl. 252-475) The present invention relates to the use as lubricants, metal-working agents and hydraulic liquids of hydroxyalkylated mercaptans. According to the invention there are used for this purpose the hydroxyalkylated mercaptans which are obtained by reacting Z-mercaptobenzthiazole or its substituted products with ethylene oxide, propylene oxide and/or epichlorhydrin in a molecular ratio of 1 to at least 5. These hydroxyalkylated 2-mercaptobenzthiazoles are applied as such or in the form of their solutions in water and/ or hydrophilic organic compounds. The above compounds and method for their preparation are known in the art. Attention is called, for instance, to Gluesenkamp, US. Patent No. 2,498,617, filed July 2, 1947, and to Harle, US. Patent No. 2,721,177, filed March 30, 1953.
As substituted products of Z-mercaptobenzthiazole are mentioned for example 5-chloro-2-mercaptobenzthiazole, 6-nitro-2-mercaptobenzthiazole and 6-methoxy-2-mercaptobenzthiazole. Among the hydrophilic organic compounds to be considered as solvents there are to be understood in the first place those which contain hydroxyl groups, carbonamide groups, carbonyl groups or ether groups. Suitable representatives are for example ethylene glycol, diethylene glycol, triethylene glycol monoacetate, dimethyl formamide, methyl ethyl ketone, furthermore polyethers such as are obtainable for example by the polymerisation of 1,2- and/or 1,4-hydroxy compounds, by polycondensation of glycols or glycol mixtures, by conversion of glycols or glycol mixtures with aliphatic dihalogen compounds or by conversion of monoor polyhydric alcohols with 1,2- and 1,4-hydroxy compounds.
The ratio between the hydroxyalkylated Z-mercaptobenzthiazoles and the solvents to be considered may vary within wide limits: in many cases a content of 0.5 percent by weight of the hydroxyalkylated Z-mercaptobenzthiazoles is sufficient. Suitable proportions can easily be ascertained as the case may be.
The hydroxyalkylated Z-mercaptob-enzthiazoles as Well as their solutions in water and/or hydrophilic organic compounds possess an excellent lubricating effect not only in the field of hydrodynamic lubrication but also in the field of maximum friction.
The hydroxyalkylated Z-mercaptobenzthiazoles in the form of their aqueous solutions can very successfully be applied in metal cutting because of their high efficacy in the field of maximum friction; they are transparent and do not lead to demixing so that the work pieces can satisfactorily be observed during treatment. The hydroxyalkylated Z-mercaptobenzthiazoles or their solutions in water and/ or hydrophilic organic compounds can also be successfully applied in non-cutting metal-working. Thanks to their good compatibility with water they can easily be removed from the work pieces after treatment is completed. It is noteworthy that the hydroxyalkylated products do not give rise to cloudiness in hard water due to the formation of insoluble calcium compounds and that they can not only be used in a neutral but also in an acidic or alkaline medium.
3,174,933 Patented Mar. 23, 1965 If desired, the agents according to the present invention can also be admixed with defoaming agents, anticorrosives or with agents increasing the viscosity of the liquids.
It is already known to use as lubricants and the like hydroxyalkylated aliphatic mercaptans, for example hydroxyalkylated dodecylmercaptan. Compared therewith the products to be used according to the invention are distinguished by a surprisingly higher efiicacy. This can be seen from the following table in which the maximum loads are indicated which result from comparative tests of the hydroxyalkylated mercaptans by the Almen-Wieland method (cf. Zerbe, Mineraloele und verwandte Produkte (1952), 907 to 908).
Table Maximum load in kg. when using Content of the hydroxyalkylated product in The hydroxyalkyla- The hydroxyalkyla' aqueous solution in perted product from 1 ted product from 1 cent by weight mol of Z-mercaptomol of dodecylbenzthiazole and mereaptan and 18 20 mol of ethylene mol of ethylene oxide oxide We claim:
1. In a process in the metal working art, the improvement consisting in applying to an object being worked a solution consisting essentially of a major amount of water and an active lubricating amount of a compound having the formula wherein X is a member selected from the group consisting of chloro and hydrogen and Y is a member selected from the group consisting of methoxy, nitro, chloro and hydrogen; when X is chloro, Y being defined as hydrogen, and when X is hydrogen, Y is defined as hydrogen, nitro, chloro and methoxy; and n is an integer of 3-18.
2. In a process in the metal working art, the improvement comprising employing as a lubricant an aqueous solution containing a major amount of Water and about .5%3% by weight of a compound having the formula 01- s-o,H.0- o,nlo) volition NO s wherein n is an integer of 3-18.
4. In a process in the metal working art, the improvement comprising employing as a lubricant an aqueous v 0 solution containing a major amount of Water and about .5 %3% by weight of a compound having the formula 5. In a process in the metal working art, the improvement comprising employing as a lubricant an aqueous solution containing a major amount of water and about .5 %3% by Weight of a compound having the formula wherein n is an integer of 3-18.
References Cited by the Examiner UNITED STATES PATENTS DANIEL E. WYMAN, Primary Examiner.
ALPHONSO D. SULLIVAN, JULIUS GREENWALD,
Examiners.

Claims (1)

1. IN A PROCESS IN THE METAL WORKING ART, THE IMPROVEMENT CONSISTING IN APPLYINT TO AN OBJECT BEING WORKED A SOLUTION CONSISTING ESSENTIALLY OF A MAJOR AMOUNT OF WATER AND AN ACTIVE LUBRICATING AMOUNT OF A COMPOUND HAVING THE FORMULA
US6377A 1959-02-18 1960-02-03 Lubricants, metal-working agents, and hydraulic liquids Expired - Lifetime US3174933A (en)

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US3505844A (en) * 1966-08-22 1970-04-14 Reynolds Metals Co Rolling lubrication
US20040152600A1 (en) * 2001-05-12 2004-08-05 Uwe Dahlmann Ether carboxylic acids based on alkoxylated mercaptobenzothiazoles and use of the same as corrosion inhibitors
US20050037931A1 (en) * 2003-08-15 2005-02-17 Rowland Robert G. Reaction products of mercaptobenzothiazoles, mercaptothiazolines, and mercaptobenzimidazoles with epoxides as lubricant additives

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US2201258A (en) * 1936-08-11 1940-05-21 Goodrich Co B F Extreme pressure lubricant
US2418499A (en) * 1944-06-20 1947-04-08 Du Pont 2-alkoxymethylmercapto-thiazoles and thiazolines and a process for preparing the same
US2498617A (en) * 1947-07-02 1950-02-21 Monsanto Chemicals Polyglycol products
US2625509A (en) * 1950-03-20 1953-01-13 Soeony Vacuum Oil Company Inc Cutting fluid and coolant
US2721177A (en) * 1953-03-30 1955-10-18 California Research Corp Poly-oxyalkylene glycol lubricant composition
US2985590A (en) * 1955-09-28 1961-05-23 Exxon Research Engineering Co Lubricating oil compositions comprising mercaptobenzothiazole ester derivatives

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US2201258A (en) * 1936-08-11 1940-05-21 Goodrich Co B F Extreme pressure lubricant
US2418499A (en) * 1944-06-20 1947-04-08 Du Pont 2-alkoxymethylmercapto-thiazoles and thiazolines and a process for preparing the same
US2498617A (en) * 1947-07-02 1950-02-21 Monsanto Chemicals Polyglycol products
US2625509A (en) * 1950-03-20 1953-01-13 Soeony Vacuum Oil Company Inc Cutting fluid and coolant
US2721177A (en) * 1953-03-30 1955-10-18 California Research Corp Poly-oxyalkylene glycol lubricant composition
US2985590A (en) * 1955-09-28 1961-05-23 Exxon Research Engineering Co Lubricating oil compositions comprising mercaptobenzothiazole ester derivatives

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3505844A (en) * 1966-08-22 1970-04-14 Reynolds Metals Co Rolling lubrication
US20040152600A1 (en) * 2001-05-12 2004-08-05 Uwe Dahlmann Ether carboxylic acids based on alkoxylated mercaptobenzothiazoles and use of the same as corrosion inhibitors
US7008561B2 (en) 2001-05-12 2006-03-07 Clariant Gmbh Ether carboxylic acids based on alkoxylated mercaptobenzothiazoles and use of the same as corrosion inhibitors
US20050037931A1 (en) * 2003-08-15 2005-02-17 Rowland Robert G. Reaction products of mercaptobenzothiazoles, mercaptothiazolines, and mercaptobenzimidazoles with epoxides as lubricant additives
US7442673B2 (en) * 2003-08-15 2008-10-28 Crompton Corporation Reaction products of mercaptobenzothiazoles, mercaptothiazolines, and mercaptobenzimidazoles with epoxides as lubricant additives
US20090076279A1 (en) * 2003-08-15 2009-03-19 Rowland Robert G Reaction products of mercaptobenzothiazoles, mercaptothiazolines, and mercaptobenzimidazoles with epoxides as lubricant additives
US8097731B2 (en) 2003-08-15 2012-01-17 Crompton Corporation Reaction products of mercaptobenzothiazoles, mercaptothiazolines, and mercaptobenzimidalzoles with epoxides as lubricant additives

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GB940781A (en) 1963-11-06

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